Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

• the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
• this invention relates to substituted 1,2,4-thiadiazolylpyrrolones and 1,2,4-thiadiazolylhydantoins and their salts, to processes for their preparation and to their use as herbicides, in particular for controlling weeds and / or weeds in crops and / or as plant growth regulators to influence the growth of
• pharmaceutical agents can be used, for example as neuroprotective agents (see Molecular Pharmaceutics, 2012, 9, 2156) or as antiviral agents (see WO2010 / 132404). Furthermore, certain substituted 1,2,4-thiadiazoles are described as pharmaceutical active ingredients for the inhibition of certain sodium channels (see WO2015 / 0218102). Various publications describe substituted pyrrolones and hydantoins with herbicides
• WO2016 / 071359 and WO2016 / 071360 disclose pyrrolones which carry heterocyclic substituents on the nitrogen, for example optionally also further substituted
• Isoxazolines Furthermore, substituted pyrrolones and their herbicidal or pesticidal properties are described in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 and EP0286816.
• WO2016 / 071361, WO2016 / 071362, WO2016 / 071363 and WO2016 / 071364 also describe substituted hydantoins which likewise carry heterocyclic substituents on the nitrogen, for example optionally further substituted isoxazolines.
• Selected specifically substituted 1,3,4-thiadiazolyl and l, 2,4-thiadiazolyl-2,5-Dioxoimidazoline and their herbicidal activity are described in DE2247266.
• Hydrox 8 ) -alkylene, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxyalkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyloxy, (C 1 - C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkoxy, (C 1 -C 8 ) -haloalkylthio, (C 3 -C 10) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, aryl, heteroaryl, (C C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkylene, heterocyclyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkenyloxy, (C 2 -C 8 ) -al
• R3 is hydroxy, Hydrothio, halogen, NR 10 R 11, (C 1 -C 8 ) -alkoxy, (C 3 -C 10 ) -cycloalkyl- (C 1 -C 8 ) -alkoxy, aryl- (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- C 1 -C 8 ) -alkoxy, arylcarbonyloxy, (C 1 -C 8 ) -alkylcarbonyloxy, aryl- (C 1 -C 8 ) -alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 10 ) -cycloalkylcarbonyloxy, NR 10 R 11, (C 1 -C 8 ) -alkoxy, (C 3 -C 10 ) -cycloalkyl- (C 1 -C 8 )
• R 5 is hydrogen, hydroxy, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -hydroxyalkyl,
• R 12 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -cyanoalkyl, (C 1 -C 10 ) Haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -C 10 ) cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -Cycloalkenyl, (C 4 -C 10 ) -halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylene, (C 1 -C 8 ) -
• R 13 is (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -cyanoalkyl, (C 1 -C 10 ) Haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -C 10 ) cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -Cycloalkenyl, (C 4 -C 10 ) -halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkylene, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkylene,
• X is oxygen or sulfur.
• cyclic structural elements in particular the structural elements aryl, cycloalkyl,
• the compounds of general formula (I) can be prepared by addition of a suitable organic compound.
• inorganic or organic acid such as mineral acids such as HCl, HBr, H2SCM, H3PCM or HNO3, or organic acids, e.g. Carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, such as p-toluenesulfonic acid, to a basic group, e.g. Amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion. Suitable substituents which are in deprotonated form, e.g. Sulfonic acids, certain
• Sulfonklareamide or carboxylic acids may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of a base
• Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
• Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
• Alkaline earth metal salts in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
• R a to R d are each independently an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Also suitable are alkylsulfonium and
• Alkylsulfoxonium salts such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
• substituted 1,2,4-thiadiazolylpyrrolones and 1,2,4-thiadiazolylhydantoins of the general formula (I) according to the invention can be used as a function of external conditions, such as pH,
• R3 is hydroxy, Hydrothio, halogen, NR 10 R 11, (C 1 -C 7 ) -alkoxy, (C 3 -C 10 ) -cycloalkyl- (C 1 -C 7 ) -alkoxy, aryl- (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- C 1 -C 7 ) alkoxy, arylcarbonyloxy, (C 1 -C 7 ) - Alkylcarbonyloxy, aryl- (C 1 -C 7) -alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 10) -cycloalkylcarbonyloxy, heterocyclic
• R6 is hydrogen, (C 1 -C 7 ) alkyl
• R 10 and R 11 are identical or different and are each independently hydrogen, (C 1 -C 7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) -alkynyl, (C 1 -C 7 ) -cyanoalkyl, (C 1 -C 10 ) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10 ) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -cycloalkenyl, (C 4 -C 10 ) -cycloalkenyl, (C 4 -C 10 ) -cycloalkenyl, (C 4 -C 10 ) -cycloalkenyl,
• R 1 is hydrogen, halogen, hydroxy, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) -alkoxy, ( C 1 -C 6) alkoxy- alkylene (C 1 -C 6), (C 1 -C 6) alkoxy (C 1 -C 6) alkyloxy, (C 1 -Ce) - haloalkoxy, (C 3 -C 10) cycloalkyl, (C3-C 6) halocycloalkyl, (C2-C6) alkenyl, (C 2 -C 6) - alkenyloxy, (C2-C6) -alkynyl, (C2-C6) alkynyloxy, heterocyclyl , Aryl, heteroaryl, tri - [(C 1 -C 8 ) -alkyl] si
• R 2 is hydrogen, halogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 1 -C 6 ) -alkoxy, (C 1 - C6) -alkoxy- (C 1 -C 6 ) -alkylene, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyloxy, (C 1 -Ce) -haloalkoxy, (C 3 -C 10 ) cycloalkyl, (C3-C 6) halocycloalkyl, (C2-C6) alkenyl, (C 2 -C 6) - alkenyloxy, (C2-C6) -alkynyl, (C2-C6) alkynyloxy, NR 10 R 11 , heterocyclyl, aryl, heteroaryl, tri- [(
• R 3 is hydroxy, Hydrothio, halogen, NR 10 R 11, (C 1 -C 6) alkoxy, (C3-C 10) cycloalkyl (C 1 -C 6) - alkoxy, aryl (C 1 -C 6 ) alkoxy, (C 1 -C 6) alkoxy (C 1 -C 6) alkoxy, arylcarbonyloxy, (C 1 -C ⁇ ) - alkylcarbonyloxy, aryl (C 1 -C 6) alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-C10 ) - Cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (C 1 -C 6) -haloalkylcarbonyloxy, (C 2 -C 6) -alkenylcarbonyloxy, OC (O) OR 12 , OC (O) SR 12 , OC (S) OR 12 , OC (S) SR 12
• R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 6) -alkyl,
• R 12 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) -cyanoalkyl, (C 1 -C 10 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (
• R 1 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1 Methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4 Methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbut
• Heterocyclyl optionally substituted phenyl, heteroaryl, 2- (trimethylsilyl) ethyn-1-yl, 2- (triethylsilyl) ethyn-1-yl, 2- (tris-iso-propylsilyl) -ethyn-1-yl,
• R 2 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl , 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl , 1,1-dimethylbutyl,
• R 3 is hydroxy, hydrothio, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, n-propyloxy, 1-
• R 4 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl , 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl
• Pentafluoroethyl 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,
• Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl , 3,3,3-trifluoro-n-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, spiro [2.2] pent-1-yl,
• R 5 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
• R 11 are the same or different and independently of one another represent hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl,
• Trifluoromethoxy-n-propyl difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2, 2-trifluoroethoxyethyl, 2,2,2-trifluoroethoxy-n-propyl,
• Pentafluoroethoxymethyl pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl,
• R 12 is methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2 Trimethylpropyl, 1-ethy
• phenyl optionally substituted phenyl, aryl (C 1 -C 6) alkyl, heteroaryl, heteroaryl (C 1 -C 6) alkyl, (C4-C6) cycloalkenyl (C 1 -C 6) alkyl, (C 1 - C6) alkoxycarbonyl (C 1 -C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (C 1 -C 6) alkyl, aryl (C 1 -C 6) alkoxycarbonyl (C 1 -C 6 ) alkyl,
• R 13 is methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2 Trimethylpropyl, 1-ethy
• Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, Difluoro-tert-butyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -halocycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6 ) -halocycloalkenyl , Methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethy
• R 1 in the grouping CR 1 and R 5 in the grouping NR 5 are each the Meanings according to the definitions below have, and further in the case where A is the group CR 1 , the adjacent group CR 2 is linked via a double bond and in the case where A is the group NR 5 , the adjacent grouping CHR 2 is linked via a single bond,
• R 1 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1 Methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1
• R 2 is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methyl-2-propenyl, prop-2-en-1-yloxy, but-3-en-1-yloxy, penta- 4-en-1-yloxy, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 1-hexynyl, prop-2- in-1-yloxy, but-3-yn-1-yloxy, but-2-yn-1-yloxy, heterocyclyl, optionally substituted phenyl, heteroaryl, 2- (trimethylsilyl) ethyn-1-yl, R 2 is hydrogen, fluorine, chlorine, bromine, iodine,
• R 3 is hydroxy, hydrothio, chloro, bromo, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2 Methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy,
• Methoxyethoxy methoxy-n-propyloxy, methoxy-n-butyloxy, ethoxymethoxy, ethoxyethoxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, heteroarylcarbonyloxy,
• Difluoromethylcarbonyloxy methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, n-bulyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, cyclopropylsulfonyloxy cyclobutylsulfonyloxy,
• Cyclopentylsulfonyloxy Cyclohexylsulfonyloxy, phenylsulfonyloxy, p-chlorophenylsulfonyloxy, m-chlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, p-fluorophenylsulfonyloxy, m- fluorophenylsulfonyloxy, o-fluorophenylsulfonyloxy, p-methoxyphenylsulfonyloxy, m- methoxyphenylsulfonyloxy, o-methoxyphenylsulfonyloxy, p-methylphenylsulfonyloxy, m- methylphenylsulfonyloxy, o -Methylphenylsulfonyloxy stands,
• R 4 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl , 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl
• Pentafluoroethyl 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,
• Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, fluoromethyl , 3,3,3-trifluoro-n-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1 Methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobut
• Trifluoromethylphenylcarbonyl methoxy, ethoxy, n-propyloxy, isopropoxy, benzyloxy, p-chlorophenylmethoxy, phenyloxy, p-chlorophenyloxy, m-chlorophenyloxy, o-chlorophenyloxy, p-fluorophenyloxy, m-fluorophenyloxy, o-fluorophenyloxy, p-methoxyphenyloxy, m-methoxyphenyloxy, o-methoxyphenyloxy, p-trifluoromethylphenyloxy, m-trifluoromethylphenyloxy, o-trifluoromethylphenyloxy, methylaminocarbonyl,
• Cyclopentylthio cyclohexylthio, phenylthio, pyrid-2-ylthio, pyrid-3-ylthio, pyrid-4-ylthio, p-chlorophenylthio, m-chlorophenylthio, o-chlorophenylthio, p-fluorophenylthio, m-fluorophenylthio,
• 0-fluorophenylthio p-methoxyphenylthio, m-methoxyphenylthio, o-methoxyphenylthio, p-methylphenylthio, m-methylphenylthio, o-methylphenylthio, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl,
• R 5 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
• Benzylmethylaminocarbonyl methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, n-butyloxycarbonylethyl, tert-butyloxycarbonylethyl, benzyloxycarbonylmethyl, methylcarbonyloxymethyl,
• Ethylcarbonyloxymethyl n-propylcarbonyloxymethyl, 1-methylethylcarbonyloxymethyl, 1,1-dimethylethylcarbonyloxymethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl,
• R6 is hydrogen
• R 10 and R 11 are identical or different and are each independently hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n pentyl,
• Trifluoromethoxy-n-propyl difluoromethoxymethyl, difluoromethoxyethyl, difluoromethoxy-n-propyl, 2,2-difluoroethoxymethyl, 2,2-difluoroethoxyethyl, 2,2-difluoroethoxy-n-propyl, 2,2,2-trifluoroethoxymethyl, 2,2, 2-trifluoroethoxyethyl, 2,2,2-trifluoroethoxy-n-propyl,
• Pentafluoroethoxymethyl pentafluoroethoxyethyl, pentafluoroethoxy-n-propyl, methylthiomethyl, methylthioethyl, ethylthioethyl, methylthio-n-propyl, ethylthio-n-propyl,
• R 12 is methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2 Trimethylpropyl, 1-ethy
• phenyl optionally substituted phenyl, aryl (C 1 -C 6) alkyl, heteroaryl, heteroaryl (C 1 -C 6) alkyl, (C4-C6) cycloalkenyl (C 1 -C 6) alkyl, (C 1 - C6) alkoxycarbonyl (C 1 -C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl (C 1 -C 6) alkyl, aryl (C 1 -C 6) alkoxycarbonyl (C 1 -C 6 ) alkyl,
• R 13 is methyl, ethyl, n -propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2 Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2 Trimethylpropyl, 1-ethy
• Nonafluorobutyl chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoro-n-propyl, Difluoro-tert-butyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 6 ) -halocycloalkyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6 ) -halocycloalkenyl , Methoxymethyl, ethoxymethyl, ethoxyethyl, methoxyethy
• phenyl optionally substituted phenyl, aryl (C 1 -C 6) alkyl, heteroaryl, heteroaryl (C 1 -C 6) alkyl, heterocyclyl (C 1 -C 6) alkyl, (C4-C6) cycloalkenyl (C 1 -C 6 ) -alkyl, NR 10 R 11 , and X is oxygen.
• R 1 is hydrogen, chlorine, bromine, iodine, hydroxy, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Trifluoromethyl, difluoromethyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, methoxymethyl, methoxymethoxy, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, ethenyl, 1-propenyl, prop-2-ene -l-yloxy, ethynyl, 1-propynyl, 1-butynyl, 1-pentynyl, 1-hexynyl, 2- (tri
• R 2 is hydrogen, chlorine, bromine, iodine, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1
• Methylpropyl 2-methylpropyl, 1,1-dimethylethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, n-propyloxy, isopropoxy, methoxymethyl, methoxymethoxy, trifluoromethoxy, difluoromethoxy, 2,2,2- Trifluoroethoxy, 2,2-difluoroethoxy, ethenyl, 1-propenyl, prop-2-en-1-yloxy, ethynyl, 1-propynyl, prop-2-yn-1-yloxy, but-3-yn-1-yloxy, But-2-yn-1-yloxy, dimethylamino, methylamino, amino,
• Ethoxyethylamino methoxyethylamino, cyclopropylamino, cyclobutylamino, 2,2-dimethylprop-1-ylamino, prop-2-yn-1-ylamino, prop-2-en-1-ylamino,
• R 3 is hydroxy, hydrothio, chloro, bromo, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2 Methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4- Methylpentylcarbon
• Methoxyethoxy methoxy-n-propyloxy, methoxy-n-butyloxy, ethoxymethoxy, ethoxyethoxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, heteroarylcarbonyloxy,
• Difluoromethylcarbonyloxy methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, n-bulyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethylpropyloxycarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, cyclopropylsulfonyloxy cyclobutylsulfonyloxy,
• Cyclopentylsulfonyloxy Cyclohexylsulfonyloxy, phenylsulfonyloxy, p-chlorophenylsulfonyloxy, m-chlorophenylsulfonyloxy, o-chlorophenylsulfonyloxy, p-fluorophenylsulfonyloxy, m- fluorophenylsulfonyloxy, o-fluorophenylsulfonyloxy, p-methoxyphenylsulfonyloxy, m- methoxyphenylsulfonyloxy, o-methoxyphenylsulfonyloxy, p-methylphenylsulfonyloxy, m- methylphenylsulfonyloxy, o -Methylphenylsulfonyloxy stands,
• R 4 is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, hydrothio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl , 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl
• Pentafluoroethyl 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl,
• Trifluoromethoxyethyl difluoromethoxyethyl, 2,2-difluoroethoxyethyl, 2,2,2-trifluoroethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, n- Butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, m-fluorophenylcarbonyl, o-fluorophenylcarbonyl, p-me
• Benzylmethylaminocarbonyl methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyanomethyl, cyanoethyl, cyano-n-propyl, hydroxycarbonyl, CHO, methoxyethylthio, ethoxyethylthio, trifluoromethoxyethylthio, pentafluoroethoxyethylthio, methylthioethylthio, ethylthioethylthio, trifluoromethylthioethylthio, pentafluorothioethylthio, benzylthio, p-chlorophenylmethylthio, m-chlorophenylmethylthio, o-chlorophenylmethylthio, p-fluorophenylmethylthio, m-flu
• R 5 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
• Cyanoethyl methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, tert-bulyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl,
• Benzylmethylaminocarbonyl methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-bulyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, n-bulyloxycarbonylethyl, tert-butyloxycarbonylethyl, benzyloxycarbonylmethyl, methylcarbonyloxymethyl,
• Ethylcarbonyloxymethyl n-propylcarbonyloxymethyl, 1-methylethylcarbonyloxymethyl, 1,1-dimethylethylcarbonyloxymethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl,
• R 6 is hydrogen
• R 3 is hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2- Dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbon
• Trifluoromethoxyethyl difluoromethoxyethyl, 2,2-difluoroethoxyethyl, 2,2,2-trifluoroethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, n- Butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-chlorophenylcarbonyl, m-chlorophenylcarbonyl, o-chlorophenylcarbonyl, p-fluorophenylcarbonyl, m- Fluorophenylcarbonyl, o-fluorophenylcarbonyl, p-me
• Benzylmethylaminocarbonyl methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyanomethyl, cyanoethyl, cyano-n-propyl, hydroxycarbonyl, CHO, methoxyethylthio, ethoxyethylthio, trifluoromethoxyethylthio, pentafluoroethoxyethylthio,
• Trifluoromethyloxyprop-2-yl 2-difluoromethyloxyprop-2-yl, 2,2,2-trifluoroethyloxyprop-2-yl, 2,2-difluoroethyloxyprop-2-yl, 2- (4-chlorophenylmethoxy) prop-2-yl, 2 - (4-fluorophenylmethoxy) prop-2-yl, 2- (4-bromophenylmethoxy) prop-2-yl, 2- (4-trifluoromethylphenylmethoxy) prop-2-yl, 2- (4-methylphenylmethoxy) prop-2-yl , 2- (3-Chlorophenylmethoxy) prop-2-yl, 2- (3-fluorophenylmethoxy) prop-2-yl, 2- (3-chlorophenylmethoxy) prop-2-yl, 2- (3-fluorophenylmethoxy) prop-2-yl, 2- (3-fluorophenylmethoxy) prop-2-yl,
• Bromophenylmethoxy) prop-2-yl 2- (3-trifluoromethylphenylmethoxy) prop-2-yl, 2- (3-methylphenylmethoxy) prop-2-yl, 2- (2-chlorophenylmethoxy) prop-2-yl, 2- (3-methylphenylmethoxy) prop-2-yl 2 Fluorophenylmethoxy) prop-2-yl, 2- (2-bromophenylmethoxy) prop-2-yl, 2- (2-trifluoromethylphenylmethoxy) prop-2-yl, 2- (2-methylphenylmethoxy) prop-2-yl,
• R 5 is hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-
• Cyanoethyl methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl,
• Benzylmethylaminocarbonyl methoxycarbonylmethyl, ethoxycarbonylmethyl, n-propyloxycarbonylmethyl, isopropyloxycarbonylmethyl, n-butyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylethyl, isopropyloxycarbonylethyl, n-butyloxycarbonylethyl, tert.
• Methoxy, ethoxy, n-propyloxy isopropoxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl, n-butyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, isopropoxyethyl, methoxy-n-propyl, ethoxy-n- propyl, methoxy-n-bulyl, or wherein R 2 and R 5 together with the N-atom or C-atom to which they respectively
• R 6 is hydrogen and X is oxygen.
• alkylsulfonyl alone or as part of a chemical group - is straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
• Carbon atoms for example (but not limited to) (C 1 -C 6) alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentyl
• Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
• alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
• Carbon atoms such as (C 1 -C 10 ), (C 1 -C 6) or (C 1 -C 4) alkylthio, for example (but not limited to) (C 1 -C 6) alkylthio, such as methylthio, ethylthio, propylthio , 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2 Dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutyl
• alkenylthio denotes an alkenyl radical bonded via a sulfur atom
• alkynylthio represents an alkynyl radical bonded via a sulfur atom
• cycloalkylthio denotes a cycloalkyl radical bonded via a sulfur atom
• cycloalkenylthio denotes an via
• Alkoxy means an alkyl radical bonded via an oxygen atom, for example (but not limited to) (C 1 -C 6) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2- Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1- Ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethylbut
• Alkenyloxy means an alkenyl group bonded via an oxygen atom
• Alkynyloxy means an alkynyl radical bound via an oxygen atom, such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10) -, (C 3 -C 6 ) - or (C 3 -C 4 ) -alkynoxy.
• Cycloalkyloxy means a cycloalkyl group bonded via an oxygen atom
• cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
• the number of carbon atoms refers to the alkyl radical in the
• the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
• the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
• the abbreviated form O shown in parentheses is a via a double bond to the adjacent carbon atom bound oxygen atom.
• the abbreviation S shown in parentheses S stands for a double bond bound to the adjacent carbon atom
• aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
• optionally substituted aryl also includes polycyclic systems, such as
• Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio, haloalkyl, alkoxy, Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl
• Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
• Arylalkoxy A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
• heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
• N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
• heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
• polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl.
• optionally substituted heterocyclyl also become
• the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two Oxygen atoms are to be directly adjacent, such as with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2 or 3-yl, 2,3- dihydro-lH-pyrrole
• Heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
• heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2 or
• 1,2-dithiin-3 or 4-yl 1,2-dithiin-3 or 4-yl; l, 2-dithiin-3 or 4-yl; l, 3-dithian-2 or 4 or 5-yl; 4H-l, 3-dithiin-2 or 4 or 5 or 6-yl; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
• heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1, 4,2-dioxazinan-2 or 3 or 5 or 6-yl; 5,6-dihydro-1,4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazine-3- or 5- or 6-yl; l, 4,2-dioxazepan-2 or 3 or 5 or 6 or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2 or 3 or 5 or 6 or 7-yl; 2,3-dihydro-5H-1, 4,2-di
• heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
• Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
• Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
• the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
• lactones and lactams are preferably also included.
• the oxo group can also occur at the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
• N (O), S (O) (also SO for short) and S (O) 2 also short SO2
• heteroaryl stands for heteroaromatic compounds, ie.
• heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; lH-pyrrol-2-yl; lH-pyrrole
• Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
• quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
• Isoquinolines e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
• quinoxaline quinazoline
• cinnoline 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine
• heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H- Indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran 5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazole
• halogen means, for example, fluorine, chlorine, bromine or iodine.
• halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
• alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted and is referred to in the latter case as “substituted alkyl".
• Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine.
• the prefix "bis” also includes the combination of different alkyl radicals, for example, methyl (ethyl) or ethyl (methyl).
• haloalkyl alkenyl and alkynyl
• alkenyl alkynyl
• alkynyl the same or different halogen atoms, partially or fully substituted alkyl, alkenyl, and alkynyl, e.g., monohaloalkyl
• ( Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. CC1 3 , CC1F 2 , CFC1 2 , CF 2 CC1F 2 , CF 2 CC1FCF 3 ; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term perhaloalkyl also encompasses the term perfluoroalkyl.
• Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
• Partially fluorinated haloalkyl means a straight-chain or branched, saturated
• Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
• halogen atoms having at least one fluorine atom, wherein all other optional halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
• the corresponding halogen atoms can be used as
• Substituents are located on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
• Partially fluorinated haloalkyl also includes the complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain.
• Haloalkoxy refers to a bonded via an oxygen atom and haloalkyl group is for example (but not limited to) OCF 3, OCHF 2, OCH 2 F, OCF2CF3, OCH2CF3 and OCH2CH2CI; same applies to haloalkenyl and other halogen-substituted radicals.
• (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the formula
• Range for C atoms includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
• General alkyl radicals having a larger specified range of carbon atoms eg. B. "(C 1 -C 6) -alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
• hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
• Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
• alkenyl in particular also includes straight-chain or branched open-chain
• Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl.
• Alkenyl is, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (C 2 -C 6) -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3 Pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl 2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl
• alkynyl in particular also includes straight-chain or branched open-chain
• C 2 -C 6) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl , 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl
• cycloalkyl means a carbocyclic, saturated ring system preferably having 3-8 ring C atoms, eg cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio , Haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
• Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
• spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl, spiro [3.3] hept-1-yl, spiro [3.3] hept-2-yl.
• Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2- Cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, substituents also having a double bond on the cycloalkenyl radical, for example an alkylidene group such as methylidene, being included
• the explanations apply to substituted Corresponding to cycloalkyl.
• alkylidene for example also in the form (C 1 -C 10 ) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond
• Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom
• arylalkyloxy means an arylalkyl radical bonded via an oxygen atom
• alkoxyalkyl s t e ht for a bound via an alkyl group and alkoxy group
• alkoxyalkoxy refers to a bonded via an oxygen atom alkoxyalkyl radical, for example (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
• Alkylthioalkyl means an alkylthio radical bonded via an alkyl group
• yyalkylthioalkylthio "means an alkylthioalkyl radical bonded via an oxygen atom.
• Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
• Heteroaryloxyalkyl means a heteroaryloxy group bonded via an alkyl group.
• Haloalkoxyalkyl means a haloalkoxy radical attached and "haloalkylthioalkyl” means a haloalkylthio radical attached via an alkyl group.
• Arylalkyl means an aryl group attached via an alkyl group
• heteroarylalkyl means a heteroaryl group bonded via an alkyl group
• heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
• Cycloalkylalkyl means a cycloalkyl group attached through an alkyl group, for example, but not limited to, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl 1-yl, 3-cyclopropylprop-1-yl.
• Arylalkenyl is an aryl radical bonded via an alkenyl group
• heteroarylalkenyl denotes a heteroaryl radical bonded via an alkenyl group
• heterocyclylalkenyl denotes a heterocyclyl radical bonded via an alkenyl group
• Arylalkynyl denotes an aryl radical bonded via an alkynyl group
• heteroarylalkynyl represents a heteroaryl group bonded via an alkynyl group
• heterocyclylalkynyl means a heterocyclyl group bonded via an alkynyl group.
• haloalkylthio alone or as part of a chemical group - is straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
• Carbon atoms such as (C 1 -C 8 ), (C 1 -C 6 ) or (C 1 -C 4) haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1 -ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
• "Halocycloalkyl” and “Halocycloalkenyl” mean by the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. B.
• cycloalkyl or cycloalkenyl for example 1-fluorocycloprop-l-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-l-yl, 1-Fluorcyclobut-l-yl, 1- Trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl,
• trialkylsilyl alone or as part of a chemical group - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
• Carbon atoms such as tri - [(C 1 -C 8 ) -, (C 1 -C 6 ) - or (C 1 -C 4 ) -alkyl] silyl, for example (but not limited to) trimethylsilyl, triethylsilyl, tri- ( n-propyl) silyl, tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, tri (2-methylprop-1-yl) silyl, Tri (1,1-dimethyleth-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl.
• tri - [(C 1 -C 8 ) -, (C 1 -C 6 ) - or (C 1 -C 4 ) -alkyl] silyl for example (but not limited to) trimethylsilyl, triethylsilyl, tri- ( n
• Trialkylsilylalkinyl stands for a trialkylsilyl radical bonded via an alkynyl group.
• the compounds of the general formula (I) can exist as stereoisomers.
• the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). If, for example, one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur.
• Stereoisomers can be distinguished from those in the
• chromatographic separation can be carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the preparation of test samples for the biological assay.
• stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
• the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof. If the compounds of general formula (I) are obtained as solids, the purification can also be carried out by recrystallization or digestion.
• Compounds of general formula (I) is prepared an optionally further substituted 5-amino-1,2,4-isothiazole (III).
• a substituted nitrile is converted into the corresponding amidine (for example with ammonia) and after halogenation with a suitable halogenating reagent (eg sodium hypochlorite or bromine) by reaction with potassium thiocyanate into the desired 5-amino-1,2,4 -isothiazole (III).
• a suitable halogenating reagent eg sodium hypochlorite or bromine
• bromochlorothiadiazole (IV) may be prepared by amination, amino-protecting (eg, with (Boc) 20, where Boc is tert-butyloxycarbonyl), followed by transition metal-mediated coupling reaction (with a suitable transition metal catalyst such as PdCl2 [P t Bu2 (FIG. p-NMe-Ph)] 2) and final acid-mediated deprotection (eg with
• Trifluoroacetic acid TFA
• a suitable polar aprotic solvent eg dichloromethane
• R 4 has the meaning previously defined.
• Substituted 1,2,4-thiadiazolylpyrrolones of the general formula (I) can be prepared in two steps by reacting a suitable optionally substituted amino-l, 2,4-thiadiazole (III) with a suitable optionally further substituted maleic anhydride (V) using a suitable Base (e.g., pyridine) in a suitable polar aprotic solvent (e.g., acetonitrile) or under acidic conditions using a suitable acid (e.g., acetic acid) and
• a suitable Base e.g., pyridine
• a suitable polar aprotic solvent e.g., acetonitrile
• a suitable acid e.g., acetic acid
• a carbonyl group of the formed substituted maleimide imide (II) are prepared.
• the reduction can be carried out in a suitable solvent (eg tetrahydrofuran and methanol) with the aid of a suitable reducing agent and can lead to regioisomers if R 1 and R 2 are different.
• suitable reducing agents are, for example, sodium hydride, calcium aluminum hydride, sodium borohydride or other hydrogen-forming metal hydrides.
• a transition metal-mediated hydrogenation can also be carried out (compare CH633678, DE2247266, WO2015 / 018434).
• Substituted 1,2,4-Thiadiazolylpyrrolone of the general formula (I) may further by
• Reducing agent eg., Lithium aluminum hydride, sodium hydride, sodium borohydride
• R 1 and R 4 have the meanings defined above
• R 2 of the general formula (I) is illustrative, but not limiting, of hydrogen, chlorine or bromine
• R 3 of the general formula (I) is exemplary but not limiting for OH
• R 6 of the general formula (I) is exemplary, but not limiting, for hydrogen.
• Substituted 1,2,4-thia diazolylhydantoins of general formula (I) may be prepared by reacting an optionally substituted amino-1, 2,4-thiadiazole (III) with a suitable optionally further substituted phenylchloroformate using a suitable base (e.g.
• Diisopropylethylamine DIPEA
• a suitable polar aprotic solvent eg dichloromethane or tetrahydrofuran
• VIII a suitable amine
• XI a substituted urea
• WO2015 / 097043 a suitable amine
• the amine in question can carry an acetal group or an ester group and thus allow the cyclization to the desired hydantoin.
• a reduction is still required to obtain the desired substituted 1,2,4-thiadiazolylhydantoin of the general formula (I).
• R 2 , R 4 and R 5 have the meanings defined above, R 3 of the general formula (I) is exemplary, but not limiting OH and R 6 of the formula (I) is exemplary, but not limiting, for Hydrogen.
• acylated with suitable reagents eg, using a suitable carbonyl chloride and with the aid of a suitable base such as triethylamine in a suitable polar aprotic solvent
• suitable base such as triethylamine in a suitable polar aprotic solvent
• sulfonylated e.g., using a suitable sulfonyl chloride and A suitable base such as triethylamine in a suitable polar aprotic solvent
• alkylated eg using a suitable alkyl halide and with Help a suitable base such as potassium carbonate, cesium carbonate or sodium hydride in a suitable polar aprotic solvent
• in a carbonate e.g, potassium carbonate, cesium carbonate or sodium hydride in a suitable polar aprotic solvent
• R 1 , R 2 and R 4 have the meanings defined above
• R 3 of the general formula (I) is by way of example but not limited to OH, OCH 3, OSO 2 CH 3 , OC (O) CH 3 and OC (0)
• OCH 3 and R 6 of the general formula (I) are exemplified by, but not limited to, hydrogen.
• No. 1.2-3 3,4-dimethyl-5-hydroxy-1- (3-ethyl-1, 2,4-thiadiazol-5-yl) -1,5-dihydro-2H-pyi-Tol-2-one
• Phenyl N - [- 3-iso-propyl-l, 2,4-thiadiazol-5-yl] carbamate (290 mg, 53% of theory) was obtained as a colorless solid.
• 1 H-NMR 400 MHz, de-DMSO ⁇ , ppm) 13.02 (s, 1H, NH), 7.49-7.44 (m, 2H), 7.34-7.27 (m, 3H), 3.10 (m, 1H), 1.29 (d, 6H).
• Phenyl N- [3-iso-propyl-l, 2,4-thiadiazol-5-yl] carbamate (290 mg, 1.10 mmol) was then dissolved in 1,4-dioxane (10 mL) without further purification and washed with 2 , 2-Dimethoxyethylmethylamine (394 mg, 3.30 mmol).
• Reaction mixture was stirred for 10 minutes at room temperature, then heated to 70 ° C and stirred for 45 minutes at a temperature of 70 ° C. After complete conversion the
• Phenyl N - [- 3-methyl-l, 2,4-thiadiazol-5-yl] carbamate (3710mg, 45% of theory) was obtained as a colorless solid.
• 1 H-NMR 400 MHz, de-DMSO ⁇ , ppm) 13.02 (s, 1H, NH), 7.51-7.44 (m, 2H), 7.36-7.27 (m, 3H), 2.45 (s, 3H).
• Phenyl N- [3-methyl-l, 2,4-thiadiazol-5-yl] carbamate 1000 mg, 4.25 mmol was then dissolved in 1,4-dioxane (20 mL) without further purification and treated with N- ( 2,2-Diethoxyethyl) propan-2-ylamine (2235 mg, 12.75 mmol).
• the reaction mixture was stirred at room temperature for 10 minutes, then heated to 70 ° C and stirred for 45 minutes at a temperature of 70 ° C. After complete conversion, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was in
• reaction mixture was stirred for 2 h at -30 ° C and then slowly warmed to room temperature. After the end of the reaction, the cautious addition of acetic acid was adjusted to pH 3-4, and water and ethyl acetate were added. The aqueous phase was repeatedly extracted intensively with ethyl acetate, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
• Citraconic anhydride 400 mg, 3.57 mmol, 1.0 equiv.
• P-toluenesulfonic acid 92 mg, 0.54 mmol
• 5-amino-3-ethyl-l, 2,4-thiadiazole 461 mg, 3.57 mmol, 1.0 equiv Toluene (12 ml) and stirred for 60 minutes under microwave conditions at a temperature of 85 ° C. After cooling to room temperature, the reaction mixture was washed with water, sat.
• Citraconic anhydride 400 mg, 3.57 mmol, 1.0 equiv
• p-toluenesulfonic acid 92 mg, 0.54 mmol
• 5-amino-3-iso-propyl-l, 2,4-thiadiazole 511 mg, 3.57 mmol, 1.0 equiv
• Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-373, in which R 4 has the meaning indicated in the respective line of Table 1. Compounds 1.1-1 to 1.1- Table 373 of Table 1.1 are thus by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-3 to 1.2-373, wherein R 4 has the meaning given in the respective line of Table 1.
• the compounds 1.2-3 to 1.2- 373 of Table 1.2 are thus by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined.
• Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-373, wherein R 4 has the meaning given in the respective line of Table 1.
• the compounds 1.3-1 to 1.3-373 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.4-1 to 1.4-373 of Table 1.4 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-373, wherein R 4 has the meaning given in the respective line of Table 1.
• the compounds 1.5-1 to 1.5-373 of Table 1.5 are thus determined by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.6-1 to 1.6-373 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.7-1 to 1.7-373 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.8-1 to 1.8-373 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-373, wherein R 4 has the meaning given in the respective line of Table 1.
• the compounds 1.9-1 to 1.9-373 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.10-1 to 1.10-373 of Table 1.10 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-373, in which R 4 has the meaning indicated in the respective line of Table 1. The compounds 1.11-1 to 1.11-373 of Table 1.11 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined. (1.12)
• Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-373, in which R 4 has the meaning given in Table 1 of each table.
• the compounds 1.12-1 to 1.12-373 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.13-1 to 1.13-373 of Table 1.13 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.14-1 to 1.14-373 of Table 1.14 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.15-1 to 1.15-373 of Table 1.15 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-3 to 1.16-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.16-3 to 1.16-373 of Table 1.16 are therefore distinguished by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined.
• Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-3 to 1.17-373, wherein R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.17-3 to 1.17-373 of Table 1.17 are thus distinguished by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined. (1.18)
• Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.18-1 to 1.18-373 of Table 1.18 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.19-1 to 1.19-373 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-3 to 1.20-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.20-3 to 1.20-373 of Table 1.20 are therefore distinguished by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined.
• Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-3 to 1.21-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.21-3 to 1.21-373 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined.
• Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.22-1 to 1.22-373 of Table 1.22 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.23-1 to 1.23-373 of Table 1.23 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined. (1.24)
• Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-373, in which R 4 has the meaning of Table 1 given in the respective line.
• the compounds 1.24-1 to 1.24-373 of Table 1.24 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-373, in which R 4 has the meaning given in Table 1 of each table.
• the compounds 1.25-1 to 1.25-373 of Table 1.25 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.26-1 to 1.26-373 of Table 1.26 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.27-1 to 1.27-373 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.28-1 to 1.28-373 of Table 1.28 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.29-1 to 1.29-373 of Table 1.29 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.30-1 to 1.30-373 of Table 1.30 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.31-1 to 1.31-373 of Table 1.31 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.32-1 to 1.32-373 of Table 1.32 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.33-1 to 1.33-373 of Table 1.33 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-373, in which R 4 has the meaning indicated in the respective line of Table 1.
• the compounds 1.34-1 to 1.34-373 of Table 1.34 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.35-1 to 1.35-373 of Table 1.35 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.36-1 to 1.36-373 of Table 1.36 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined. (1-37)
• Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.37-1 to 1.37-373 of Table 1.37 are thus characterized by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.38-1 to 1.38-373 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.39-1 to 1.39-373 of Table 1.39 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined. (1.40)
• Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.40-3 to 1.40-373 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 3 to 373 for R 4 of Table 1 defined.
• Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-373, in which R 4 has the meaning given in Table 1 of each Table.
• the compounds 1.41-1 to 1.41-373 of Table 1.41 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-373, in which R 4 has the meaning of Table 1 given in the respective line.
• the compounds 1.42-1 to 1.42-373 of Table 1.42 are therefore distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-373, in which R 4 has the meaning of Table 1 given in the respective line.
• the compounds 1.43-1 to 1.43-373 of Table 1.43 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-373, in which R 4 has the meaning of Table 1 given in the respective line.
• the compounds 1.44-1 to 1.44-373 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to 373 for R 4 of Table 1 defined.
• the 1 H NMR data of selected examples are noted in terms of 1 H NMR peaks. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
• the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; ⁇
• connection signals in the delta range of
• Solvent peaks for example peaks of DMSO in DMSO-D ⁇ and the peak of water, which are usually high in average intensity.
• the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity than the peaks of the target compounds (for example with a purity of> 90%).
• Such stereoisomers and / or impurities may be typical of each
• An expert who calculates the peaks of the target compounds using known methods can, if necessary, calculate the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if necessary, calculate the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if necessary, calculate the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if necessary, calculate the peaks of the target compounds using known methods.
• Isolate target compounds optionally with additional intensity filters are used. This isolation would be similar to peak picking in classical 1H NMR interpretation. Further details on 1 H NMR peaks can be found in Research Disclosure Database Number 564025.
• the present invention furthermore relates to the use of one or more
• the present invention furthermore relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one which is characterized as being preferred or particularly preferred
• Embodiment in particular one or more compounds of the formulas (1.1) to (1.44) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, on the (harmful) plants, (harmful) plant seeds, the soil , in which or on which the (harmful) plants grow, or the cultivated area is applied.
• the present invention also provides a method for controlling undesirable plants, preferably in crops, characterized in that an effective amount of one or more compounds of general formula (I) and / or their salts, as defined, preferably in one of the preferred or particularly preferably marked Embodiment, in particular one or more compounds of formulas (1.1) to (1.44) and / or their salts, each as defined above, or an agent according to the invention, as defined below, on undesirable plants (eg harmful plants such as mono- or dicotyledonous weeds or unwanted Crops), the seed of the undesirable plants (ie, plant seeds, eg, grains, seeds or vegetative propagules such as tubers or sprouts with buds), the soil in which or on which the undesirable plants grow (eg, the soil of cultivated land or non-cultivated land ) or the area under cultivation (ie area on which the unwanted plants will grow) is applied.
• undesirable plants eg harmful plants such as mono- or dicotyledonous weeds or unwanted Crops
• the seed of the undesirable plants
• the present invention is also a method for controlling
• Embodiment in particular one or more compounds of the formulas (1.1) to (1.44) and / or salts thereof, each as defined above, or an agent according to the invention, as defined below, the plant, the seed of the plant (ie plant seeds, eg grains, Seeds or vegetative
• Propagating organs such as tubers or sprouts with buds
• the soil in which or on which the plants grow e.g., the soil of cultivated land or non-cultivated land
• the cultivated area i.e., area on which the plants will grow
• the compounds according to the invention or the agents according to the invention may e.g. in Vorsaat- (possibly also by incorporation into the soil), pre-emergence and / or Nachauflaufmaschine be applied.
• Vorsaat- possibly also by incorporation into the soil
• pre-emergence and / or Nachauflaufmaschine be applied.
• some representatives of mono- and dicots may be applied.
• Called weed flora which can be controlled by the compounds of the invention, without the mention should be limited to certain species.
• the compounds of formula (I) and / or their salts according to the invention are suitable for controlling the following genera of monocotyledonous and dicotyledonous harmful plants:
• the compounds according to the invention are applied to the surface of the earth (weeds and / or weeds) prior to germination (pre-emergence method), either the emergence of the weed seedlings or weed seedlings is completely prevented or they grow up to the cotyledon stage, but then grow and eventually die off after three to four weeks.
• the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that in this way a weed competition harmful to the crop plants occurs very early and sustainably eliminated.
• the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotylic cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not damaged at all.
• the present compounds are very well suited for the selective control of undesired plant growth in crops such as
• the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented. Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
• the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi,
• Bacteria or viruses Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
• transgenic cultures is the use of the compounds of the invention and / or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
• cereals such as wheat, barley, rye, oats, millet, rice and maize or also crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetables.
• the compounds of the invention may also be used as herbicides in
• Crop plants are used, which are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
• the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
• the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
• Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
• Other particular properties may include tolerance or resistance to abiotic stressors, e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
• abiotic stressors e.g. Heat, cold, drought, salt and ultraviolet radiation are present.
• the compounds of the formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
• nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences.
• Base exchanges are made, partial sequences removed or natural or synthetic sequences added.
• For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments.
• the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
• DNA molecules can be used which comprise the entire coding sequence of a gene product including any flanking sequences, as well as DNA molecules which comprise only parts of the coding sequence, which parts have to be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
• the synthesized protein may be located in any compartment of the plant cell.
• the coding region is linked to DNA sequences which ensure localization in a particular compartment.
• sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227).
• the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
• the transgenic plant cells can be regenerated to whole plants by known techniques.
• the transgenic plants can in principle be plants of any one
• Plant species i. both monocotyledonous and dicotyledonous plants.
• the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth factors, such as e.g. Dicamba or against herbicides, the essential
• Plant enzymes e.g. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogues.
• ALS Acetolactate synthases
• EPSP synthases glutamine synthases
• HPPD hydroxyphenylpyruvate dioxygenases
• the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
• the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention and / or salts thereof as herbicides for controlling harmful plants in crops of useful or ornamental plants, optionally in transgenic crop plants.
• cereals preferably corn, wheat, barley, rye, oats, millet, or rice, in the pre- or post-emergence.
• Preference is also the use in soy in the pre or postemergence.
• Growth regulation of plants also includes the case where the active ingredient of formula (I) or its salt is formed from a prodrug only after plant, plant or soil application.
• the invention also provides the use of one or more compounds of the formula (I) or salts thereof or an agent according to the invention (as defined below) (in a
• Method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of general formula (I) or their salts on the plants (harmful plants, optionally together with the crops) plant seeds, the soil , in which or on which the plants grow, or the cultivated area is applied.
• the invention also provides a herbicidal and / or plant growth-regulating agent, characterized in that the agent (a) contains one or more compounds of the general formula (I) and / or salts thereof as defined above, preferably in one of the preferred or particularly preferably marked
• Embodiment in particular one or more compounds of the formulas (1.1) to (1.77) and / or salts thereof, each as defined above,
• the other agrochemically active substances of constituent (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 are mentioned.
• a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more plant protection formulation auxiliaries (ii) selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
• auxiliaries selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorptive, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water
• the compounds of the general formula (I) according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
• the invention therefore also relates to herbicidal and plant growth-regulating agents which contain compounds of the general formula (I) and / or salts thereof.
• the compounds of the general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions .
• WP wettable powder
• SP water-soluble powders
• EC emulsifiable concentrates
• EW emulsions
• sprayable solutions such as oil-in-water and water-in-oil emulsions, sprayable solutions .
• SC Suspension concentrates
• granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
• Microcapsules and waxes are Microcapsules and waxes.
• Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, have a dilution or inert or ionic and / or nonionic surfactants (wetting agents, dispersants), eg polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium,
• the herbicidal active compounds are finely ground
• emulsifiers can be used for example: Alkylarylsulfonsaure calcium salts such as
• Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol ester
• Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or
• Polyoxethylenesorbitanester such as Polyoxyethylene. Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
• Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
• Suspension concentrates may be water or oil based. They can be prepared, for example, by wet milling using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
• Emulsions e.g. Oil-in-water emulsions (EW), for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvent
• Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable adhesives, for example polyvinyl alcohol, sodium polyacrylate or mineral oils, to the surface of carriers such as sand, kaolinites or granulated inert material. Also suitable
• Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
• the agrochemical compositions preferably herbicidal or plant growth regulating agents of the present invention, preferably contain a total amount of from 0.1 to 99% by weight, preferably from 0.5 to 95% by weight, more preferably from 1 to 90% by weight, most preferably 2 to 80 wt .-%, of active compounds of the general formula (I) and their salts.
• the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
• the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
• Formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of
• Active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
• the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
• the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
• the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
• formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. DA Knowles, Kluwer Academic Publishers (1998).
• the compounds of general formula (I) or their salts may be used as such or in the form of their formulations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
• Growth regulators can be used in combination, e.g. as finished formulation or as
• Tank mixes The combination formulations can be prepared on the basis of the above-mentioned formulations, taking into account the physical properties and stabilities of the active ingredients to be combined.
• combination partners for the compounds of general formula (I) according to the invention in mixture formulations or in the tank mix are known active compounds which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase are based, can be used, such as in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc.
• cereals wheat, barley, rye, corn, rice, millet
• sugar beet wheat, barley, rye, corn, rice, millet
• herbicide and the effectiveness of each safener may vary within wide limits, for example in the range of 200: 1 to 1: 200, preferably 100: 1 to 1: 100, especially 20: 1 to 1: 20.
• the safeners can be formulated analogously to the compounds (I) or mixtures thereof with other herbicides / pesticides and provided and used as ready-to-use formulation or tank mixture with the herbicides.
• the commercially available herbicidal or herbicidal safener formulations are optionally diluted in a conventional manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water.
• Powdery e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water.
• Preparations, soil or spreading granules and sprayable solutions are usually no longer diluted with other inert substances before use.
• the total amount of compounds of the formula (I) and their salts is preferably in the range of 0.001 to 10.0 kg / ha, preferably in the range of 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, more preferably in the range of 0.05 to 1 kg / ha. This applies both to pre-emergence or post-emergence applications.
• Plant growth regulator for example as Halmverkürzer in crops, as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range of 0.001 to 2 kg / ha, preferably in the range of 0.005 to 1 kg / ha, in particular in the range of 10 to 500 g / ha, most preferably in the range of 20 to 250 g / ha. This applies to both the application in the
• Halmverkürzer Pre-emergence or postemergence.
• the application as Halmverkürzer can be done in various stages of growth of the plants. For example, the application is preferred after placement at the beginning of
• seed treatment when used as a plant growth regulator, seed treatment may be considered, including the different seed dressing and coating techniques.
• the application rate depends on the individual techniques and can be determined in preliminary tests.
• known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvyl shikimate 3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II or
• Protoporphyrinogen oxidase can be used, as e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and cited therein.
• ISO International Organization for Standardization
• herbicidal mixture partners examples include:
• flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazine, fluometuron, flurenol, flurenol-butyl, - dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meplyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfiiron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-p-
• methabenzothiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
• met.zthiazuron methiopyrsulfuron, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron ester, MT-5950, ie N- [3-chloro -4- (1-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiar
• plant growth regulators as possible mixing partners are:
• S 1 d compounds of the type of triazolecarboxylic acids (S 1 d ), preferably compounds such as
• Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
• PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
• TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
• RA 1 (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl, where the latter two radicals are represented by VA
• RA 2 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; mA 1 or 2;
• V A is 0, 1, 2 or 3;
• S4 b) Compounds of the 4- (benzoylsulfamoyl) benzamide of the formula (S4 b) and salts thereof, as they are in the WO-A-99/16744 describes
• RB 1 , RB 2 are independently hydrogen, (C 1 -C 6) alkyl, (C 3 -C 6) cycloalkyl,
• RB 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy and ms is 1 or 2, for example those where
• RB cyclopropyl
• RB ethyl
• RB isopropyl
• RB 1 isopropyl
• R B 2 hydrogen
• (RB 3 ) 2-OMe (S4-5);
• Rc 1 , Rc 2 independently of one another are hydrogen, (C 1 -C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C 3 -C 8 ) alkyl,
• Rc 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 and mc is 1 or 2; for example
• R D 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; mD 1 or 2;
• R D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl.
• S5 active ingredients from the class of hydroxyaromatic and aromatic-aliphatic
• Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1), Diphenylmethoxyessigklareethylester or Diphenylmethoxyessigklare as described in WO-A-98/38856.
• RD 1 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy, R D 2 is hydrogen or (C 1 -C 4 ) alkyl,
• RD 3 is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals is unsubstituted or substituted by one or more, preferably to substituted into three identical or different radicals from the group consisting of halogen and alkoxy; or their salts, nD is an integer from 0 to 2.
• RE 1 is halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 YE, ZE independently of one another are O or S, ⁇ is an integer from 0 to 4,
• RE 2 (C 1 -C 16 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (C 1 -C 6) alkyl.
• oxyimino compound type compounds known as seed dressing agents, such as, for example, B.
• Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmemoxyimino (phenyl) acetonitrile) (Sl 1-1), which is known as a seeding safener for millet against damage by metolachlor,
• Fluorofenim (1- (4-chloro-henyl) -2,2,2-trifluoro-1-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2) is known as a seed safener for millet against damage by metolachlor, and
• Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage from metolachlor.
• Isothiochromanone (S12) class agents e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds of WO-A- 1998/13361.
• Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
• Cyanamide which is known as safener for maize against damage by imidazolinones
• MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
• RH 1 is a (C 1 -C 6) haloalkyl radical and RH 2 is hydrogen or halogen and
• RH 3, RH 4 are independently hydrogen, (C 1 -C 1 6) alkyl, (C2-C 1 6) alkenyl or (C2-C1 6) alkynyl, where each of the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkylthio, (C 1 -C 4) alkylamino, di [(C 1 -C 4 ) alkyl] amino, [(C 1 -C 4 ) alkoxy] carbonyl, [(C 1 -C 4 ) haloalkoxy] carbonyl, (C 3 -C 6 ) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsub
• (C 3 -C 6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, or denotes RH 3 (C 1 -C 4) alkoxy, (C 2 -C 4) alkenyloxy, (C 2 -C 6) alkynyloxy or (C 2 -C 4) haloalkoxy and
• RH 4 is hydrogen or (C 1 -C 4) -alkyl or
• RH 3 and RH 4 together with the directly attached N atom form a four- to eight-membered one
• heterocyclic ring which preferably can contain up to two further hetero ring atoms from the group N, O and S in addition to the N atom, further hetero ring atoms and which is unsubstituted or substituted by one or more radicals from the group halogen, cyano, nitro, (C 1 - C 4 ) alkyl, (C 1 -C 4 ) haloalkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 ) haloalkoxy and (C 1 -C 4 ) alkylthio is substituted means.
• Preferred safeners in combination with the compounds according to the invention of the formula (I) and / or salts thereof, in particular with the compounds of the formulas (1.1) to (1.44) and / or salts thereof are: cloquintocet-mexyl, cyprosulfamide, fenchlorazole ethyl ester, isoxadifen and particularly preferred safeners are: cloquintocetmexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
• compounds of the general formula (I) according to the invention have a good herbicidal activity against harmful plants during post-emergence treatment, such as, for example, B.
• Alopecurus myosuroides Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvulus, Stellaria media, Viola tricolor, Veronica persica, Pharitis purpurea and Hoerdeum murinum at an application rate of 1.28 kg
• Seeds of monocotyledonous and dicotyledonous weeds and crop plants were placed in plastic or organic plant pots and covered with soil.
• the compounds according to the invention formulated as wettable powders (WP) or as emulsion concentrates (EC) were then applied to the surface of the cover soil as an aqueous suspension or emulsion with the addition of 0.5% of additive at a rate of 600 l / ha.
• WP wettable powders
• EC emulsion concentrates
• Tables Bl to B15 are the effects of selected compounds of general formula (I) according to Tables 1.1 to 1.44 on various harmful plants and a Application rate corresponding to 1280 g / ha or 320 g / ha, which were obtained according to the previously mentioned test procedure, shown.
• compounds of the general formula (I) according to the invention have a good herbicidal activity against harmful plants in the case of pre-emergence treatment, eg. B. harmful weeds such as Alopecurus myorsuroides, Echinochloa crus-galli, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Matricaria inodora, Polygonum convolvulus, Stellaria media, Viola tricolor, Veronica persica, Pharitis purpurea, Hordeum murinum Lolium rigidum Poa annua and Cyperus esculentus at an application rate of 1.28 kg of active ingredient or less per hectare.
• some of the compounds of the invention leave graminaceous crops such as barley, wheat, rye, millet, corn rice or sugarcane in the pre-emergence process even at high temperatures
• Chilled fresh spinach leaves were minced and suspended in 50 mM phosphate buffer, pH 6.8. 10 mM KCl, 0.34 M sucrose (sucrose buffer), homogenized (blender, 1 g of plant material / ml).
• the membrane suspension was aliquoted and frozen in liquid nitrogen. The aliquots were stored at -80 ° C. The photosystem II preparation was storage-stable for at least three months under these conditions. The activity determination of the photosystem II (PS II) was then carried out according to the following test principle:
• the enzyme-catalyzed reduction of the DCPIP led to a colorless leuco form, which led to a decrease in absorbance at 595 nm in the reaction mixture, which was measured as a function of time.
• the activity is determined in microtiter plates (96 wells) in a reaction volume of 200 ⁇ . 155 ⁇ of diluted membrane suspension in 50 mM phosphate buffer, pH 6.8, 10 mM KCl, were introduced.
• 5 ⁇ solutions of the test compounds were added at a concentration of 100 ⁇ in DMSO; Controls contained 5 ⁇ M DMSO; the

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